The present invention relates to hydrogenation of epoxides to obtain alcohols.
The cleavage of epoxides to make new compounds containing a hydroxyl group is in general known in the art. See, for example, Morrison & Boyd, "Organic Chemistry," 2d Ed., at pp. 877-992.
A. Kotz and K. Righter in an article in J. Prakt. Chem. [2 ] 111, 373 (1925) disclose hydrogenation of an epoxide to obtain a secondary alcohol, as follows: ##STR1##
Park and Fuchs state in J. Org. Chem., January 1957, at page 93: "Only a few oxides with electron-withdrawing groups have been hydrogenated, and a secondary alcohol is always produced. Glycidol, epichlorohydrin, and butadiene dioxide are reduced to 1,2-propanediol, 1-chloro-2-propanol, and 2,3-butanediol, respectively, as the main product."
Searles and Butler in JACS, Vol. 76, p. 56 (1954), disclose reduction of 1-chloro-2,3-epoxy propane using hydrogen and a nickel catalyst. The product obtained is 1-chloro-2-propanol, that is, the epoxy group was reduced to result in the OH group being on the secondary rather than the primary carbon atom.
However, Newman, Underwood and Renoll in JACS, Vol. 71, p. 3362 (1949) disclose reduction of 1,2-epoxy decane using a nickel catalyst to obtain primary decane alcohol.